US8124965B2 - Opto-electrical devices and methods of making the same - Google Patents

Opto-electrical devices and methods of making the same Download PDF

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US8124965B2
US8124965B2 US12/444,102 US44410207A US8124965B2 US 8124965 B2 US8124965 B2 US 8124965B2 US 44410207 A US44410207 A US 44410207A US 8124965 B2 US8124965 B2 US 8124965B2
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polymer
cross
layer
light
emissive
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US20100133566A1 (en
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Carl Towns
Ilaria Grizzi
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CDT Oxford Ltd
Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/151—Copolymers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K99/00—Subject matter not provided for in other groups of this subclass
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/115—Polyfluorene; Derivatives thereof

Definitions

  • One class of opto-electrical devices is that using an organic material for light emission or detection.
  • the basic structure of these devices is a light emissive organic layer, for instance a film of a poly (p-phenylenevinylene) (“PPV”) or polyfluorene, sandwiched between a cathode for injecting negative charge carriers (electrons) and an anode for injecting positive charge carriers (holes) into the organic layer.
  • PSV poly (p-phenylenevinylene)
  • polyfluorene sandwiched between a cathode for injecting negative charge carriers (electrons) and an anode for injecting positive charge carriers (holes) into the organic layer.
  • the electrons and holes combine in the organic layer generating photons.
  • the organic light-emissive material is a polymer.
  • the organic light-emissive material is of the class known as small molecule materials, such as (8-hydroxyquinoline) aluminium (“Alq3”).
  • small molecule materials such as (8-hydroxyquinoline) aluminium (“Alq3”).
  • Alq3 (8-hydroxyquinoline) aluminium
  • one of the electrodes is transparent, to allow the photons to escape the device.
  • a typical organic light-emissive device is fabricated on a glass or plastic substrate coated with a transparent anode such as indium-tin-oxide (“ITO”).
  • ITO indium-tin-oxide
  • a layer of a thin film of at least one electroluminescent organic material covers the first electrode.
  • a cathode covers the layer of electroluminescent organic material.
  • the cathode is typically a metal or alloy and may comprise a single layer, such as aluminium, or a plurality of layers such as calcium and aluminium.
  • holes are injected into the device through the anode and electrons are injected into the device through the cathode.
  • the holes and electrons combine in the organic electroluminescent layer to form an exciton which then undergoes radiative decay to give light.
  • the hole injecting layer may comprise a conductive polymer such as PEDOT:PSS.
  • the hole transport layer may comprise a semiconductive polymer such as a copolymer of fluorene and triarylamine repeat units.
  • the organic light-emissive layer may comprise a small molecule, a dendrimer or a polymer and may comprise phosphorescent moieties and/or fluorescent moieties.
  • blends in an opto-electrical device was proposed to have several advantages over the provision of multiple layers of material, it has been found that there are several problems with the use of blends in opto-electrical devices. It can be difficult to control the structure and properties of a blend. For example, the inter-mixing of materials in a blend can be difficult to control and may be unstable due to movement of chemical species within the blend, particularly when a device is driven. Provision of the different species in a single molecule can help to prevent differential movement of the species during driving of the device. However, multiple component polymers can be more difficult to make.
  • cross-linkable, hole transporting monomers can be mixed with light-emissive monomers, polymerised to form a polymer which has both the hole transporting monomers and the light-emissive monomers therein, deposited, and then cross-linked to form a light emissive layer on which an electron transporting layer can be deposited without dissolving the light-emissive layer.
  • Bozano et al J. Appl. Phys. 2003, 94(5), 3061-3068 discloses cross-linked two-component blends for organic light-emitting devices.
  • the present inventors have realized that it would be desirable to provide an arrangement in which the beneficial features of using a blend are present, but where the detrimental features are avoided.
  • the first and second polymers are different.
  • stable morphology can be achieved by using a functional group to cross-link between polymers in an organic film, i.e. to achieve a single cross-linked matrix comprising two or more polymers in a blend.
  • a functional group to cross-link between polymers in an organic film, i.e. to achieve a single cross-linked matrix comprising two or more polymers in a blend.
  • this can be a rather crude method and the chemistry used is very often indiscriminate resulting in ill-defined structures. The indiscriminate nature of the chemistry could also mean that one has little control over the process.
  • the other of the charge transporting polymer and the light-emissive polymer is also cross-linked providing a second cross-linked matrix which is disposed through the first cross-linked matrix as a continuous phase, whereby the first cross-linked matrix and the second cross-linked matrix provide an interpenetrating network. Again, there is little or no cross-linking between the two polymers.
  • WO 2006/043087 involves the separate deposition of two layers; a hole transport layer and a light-emissive layer, in order to provide a stable system.
  • a blend of two cross-linkable systems, or one cross-linkable and one non-cross-linkable system provides a stable blend morphology whilst depositing organic material only once.
  • a layer of charge injecting material such as hole injecting material, may be disposed between the layer of organic material and the first electrode to aid charge injection into the layer of organic material.
  • the charge injecting material may comprise a conductive polymer such as doped PEDOT, preferably PEDOT:PSS.
  • the first and second polymers are preferably semi-conductive conjugated polymers.
  • the difference in wavelength between an emission maximum of the first polymer and an absorption maximum of the second polymer is greater than 30 nm.
  • a method of manufacturing an opto-electrical device comprising: depositing, over a substrate comprising a first electrode for injecting charge carriers of a first polarity, a mixture of a first and a second polymer in a solvent; cross-linking the first polymer to form a first cross-linked matrix in which the second polymer is disposed; and depositing a second electrode for injecting charge carriers of a second polarity.
  • an opto-electrical device comprising: a first electrode for injecting charge carriers of a first polarity; a second electrode for injecting charge carriers of a second polarity; a layer of organic material disposed between the first and second electrodes, the layer of organic material comprising a blend of a first charge transporting and/or light-emissive polymer and a second charge transporting and/or light emissive polymer, at least the first polymer being cross-linked to provide a first cross-linked matrix in which the second polymer is disposed; and an emissive layer formed over the layer of organic material.
  • the partially crosslinked first polymer provides a surface that is stable against dissolution, and yet provides a laterally porous structure into which the charge transporting and/or light-emissive material is at least partially absorbed before being “locked in” by the further crosslinking step.
  • the opto-electrical device is an organic light-emitting device comprising an organic light emitting layer.
  • the first and second charge transporting materials are hole transporting materials.
  • the organic light-emitting layer may be deposited from solution onto the layer of organic material comprising the first and second charge transporting materials.
  • the first electrode according to any of the aforementioned aspects of the invention is an anode and the second electrode is a cathode.
  • crosslinkable polymers described above may be deposited directly onto the first electrode. However, in the case where the first electrode is the anode, it is preferable that a layer of hole injection material is provided between the anode and the crosslinkable polymer.
  • FIG. 1 shows an organic light-emissive device according to an embodiment of the present invention.
  • Further layers may be located between anode 2 and cathode 3 , such as charge transporting, charge injecting or charge blocking layers.
  • a conductive hole injection layer formed of a doped organic material located between the anode 2 and the light-emissive layer 3 to assist hole injection from the anode into the layer or layers of semiconducting polymer.
  • doped organic hole injection materials include doped poly(ethylene dioxythiophene) (PEDOT), in particular PEDOT doped with polystyrene sulfonate (PSS) as disclosed in EP 0901176 and EP 0947123, or polyaniline as disclosed in U.S. Pat. No. 5,723,873 and U.S. Pat. No. 5,798,170.
  • Hole injection layers comprising inorganic materials may also be employed, for example transition metal oxides such as molybdenum oxide.
  • Light-emissive layer 3 comprises a light-emissive polymer blended with a charge transporting polymer, at least one of the charge transporting polymer and the light-emissive polymer being cross-linked to provide a first cross-linked matrix in which the other of the charge transporting polymer and the light-emissive polymer is disposed.
  • a further light-emissive layer may be deposited over light-emissive layer 3 to provide a device wherein emission from the device arises from both light-emissive layer 3 and the further light-emissive layer, for example in order to produce white light.
  • Polymers may comprise a first repeat unit selected from arylene repeat units, in particular: 1,4-phenylene repeat units as disclosed in J. Appl. Phys. 1996, 79, 934; fluorene repeat units as disclosed in EP 0842208; indenofluorene repeat units as disclosed in, for example, Macromolecules 2000, 33(6), 2016-2020; and spirofluorene repeat units as disclosed in, for example EP 0707020.
  • substituents include solubilising groups such as C 1-20 alkyl or alkoxy; electron withdrawing groups such as fluorine, nitro or cyano; and substituents for increasing glass transition temperature (Tg) of the polymer.
  • Particularly preferred polymers comprise optionally substituted, 2,7-linked fluorenes, most preferably repeat units of formula:
  • R 1 and R 2 are independently selected from hydrogen or optionally substituted alkyl, alkoxy, aryl, arylalkyl, heteroaryl and heteroarylalkyl. More preferably, at least one of R 1 and R 2 comprises an optionally substituted C 4 -C 20 alkyl or aryl group.
  • a homopolymer of the first repeat unit such as a homopolymer of 9,9-dialkylfluoren-2,7-diyl, may be utilised to provide electron transport.
  • Particularly preferred hole transporting polymers of this type are AB copolymers of the first repeat unit and a triarylamine repeat unit.
  • the different regions within such a polymer may be provided along the polymer backbone, as per U.S. Pat. No. 6,353,083, or as groups pendant from the polymer backbone as per WO 01/62869.
  • the light-emissive polymer is cross-linked to provide a cross-linked matrix in which the charge transporting polymer is disposed, then the light-emissive polymers must be functionalised with a suitable cross-linking group such as BCB or a vinyl group.
  • the charge transporting polymer is cross-linked to provide a cross-linked matrix in which the light-emissive polymer is disposed, then the charge transporting polymers must be functionalised with a suitable cross-linking group such as BCB or a vinyl group.
  • both the charge transporting polymer and the light-emissive polymer are cross-linked providing a first cross-linked matrix and a second cross-linked matrix, whereby the first cross-linked matrix and the second cross-linked matrix provide an interpenetrating network, then both the charge transporting polymer and the light-emissive polymer must be functionalised with a suitable cross-linking group such as BOB or a vinyl group.
  • a suitable cross-linking group such as BOB or a vinyl group.
  • hosts are described in the prior art including homopolymers such as poly(vinyl carbazole) disclosed in, for example, Appl. Phys. Lett. 2000, 77(15), 2280; polyfluorenes in Synth. Met. 2001, 116, 379, Phys. Rev. B 2001, 63, 235206 and Appl. Phys. Lett. 2003, 82(7), 1006; poly[4-(N-4-vinylbenzyloxyethyl, N-methylamino)-N-(2,5-di-tert-butylphenylnapthalimide] in Adv. Mater. 1999, 11(4), 285; and poly(para-phenylenes) in J. Mater. Chem. 2003, 13, 50-55. Copolymers are also known as hosts.
  • the aforementioned polymer host materials may be functionalised with a cross-linkable group in order to provide a cross-linked charge transporting polymer matrix as a host material in which an emissive polymer is disposed.
  • Preferred metal complexes comprise optionally substituted complexes of formula (V): ML 1 q L 2 r L 3 s (V)
  • M is a metal; each of L 1 , L 2 and L 3 is a coordinating group; q is an integer; r and s are each independently 0 or an integer; and the sum of (a. q)+(b. r)+(c.s) is equal to the number of coordination sites available on M, wherein a is the number of coordination sites on L 1 , b is the number of coordination sites on L 2 and c is the number of coordination sites on L 3 .
  • Heavy elements M induce strong spin-orbit coupling to allow rapid intersystem crossing and emission from triplet states (phosphorescence).
  • Suitable heavy metals M include:
  • lanthanide metals such as cerium, samarium, europium, terbium, dysprosium, thulium, erbium and neodymium;
  • d-block metals in particular those in rows 2 and 3 i.e. elements 39 to 48 and 72 to 80, in particular ruthenium, rhodium, palladium, rhenium, osmium, iridium, platinum and gold.
  • the d-block metals form organometallic complexes with carbon or nitrogen donors such as porphyrin or bidentate ligands of formula (VI):
  • Ar 4 and Ar 5 may be the same or different and are independently selected from optionally substituted aryl or heteroaryl; X 1 and Y 1 may be the same or different and are independently selected from carbon or nitrogen; and Ar 4 and Ar 5 may be fused together.
  • Ligands wherein X 1 is carbon and Y 1 is nitrogen are particularly preferred.
  • ligands suitable for use with d-block elements include diketonates, in particular acetylacetonate (acac); triarylphosphines and pyridine, each of which may be substituted.
  • Main group metal complexes show ligand based, or charge transfer emission.
  • the emission colour is determined by the choice of ligand as well as the metal.
  • the host material and metal complex may be combined in the form of a physical blend.
  • the metal complex may be chemically bound to the host material.
  • the metal complex may be chemically bound as a substituent attached to the polymer backbone, incorporated as a repeat unit in the polymer backbone or provided as an end-group of the polymer as disclosed in, for example, EP 1245659, WO 02/31896, WO 03/18653 and WO 03/22908.
  • Suitable ligands for di or trivalent metals include: oxinoids, e.g.
  • oxygen-nitrogen or oxygen-oxygen donating atoms generally a ring nitrogen atom with a substituent oxygen atom, or a substituent nitrogen atom or oxygen atom with a substituent oxygen atom such as 8-hydroxyquinolate and hydroxyquinoxalinol-10-hydroxybenzo (h) quinolinato (II), benzazoles (III), schiff bases, azoindoles, chromone derivatives, 3-hydroxyflavone, and carboxylic acids such as salicylato amino carboxylates and ester carboxylates.
  • repeat units and end groups comprising aryl groups as illustrated throughout this application may be derived from a monomer carrying a suitable leaving group.
  • a single polymer or a plurality of polymers may be deposited from solution to form layer 5 .
  • Suitable solvents for polyarylenes, in particular polyfluorenes, include mono- or poly-alkylbenzenes such as toluene and xylene.
  • Particularly preferred solution deposition techniques are spin-coating and inkjet printing.
  • Spin-coating is particularly suitable for devices wherein patterning of the electroluminescent material is unnecessary—for example for lighting applications or simple monochrome segmented displays.
  • the polymers may be deposited in a common solvent to form a graded interface. If the polymers are left for a predetermined length of time, the polymer with the higher affinity for the underlying layer will preferentially diffuse towards the underlying layer forming a concentration gradient. One of both of the polymers may then be cross-linked to “freeze” the morphology thus forming a stable graded interface.
  • polymers comprising amine repeat units may show an affinity for an underlying acidic layer such as a hole injection a layer of PEDOT doped with an acid such as PSS.
  • a hole transporting polymer may be provided with polar end-groups and/or substituents such that the hole transporting polymer is attracted to an underlying polar hole injection layer, such as REDOT/PSS.
  • Another factor influencing phase separation may be molecular weight of the polymers.
  • a low molecular weight polymer may be more mobile, and may therefore segregate from the other polymer(s) to a greater extent than a corresponding higher molecular weight material.
  • the cathode preferably has a workfunction of less than 3.5 eV, more preferably less than 3.2 eV, most preferably less than 3 eV.
  • the device is preferably encapsulated with an encapsulant (not shown) to preventingress of moisture and oxygen.
  • encapsulants include a sheet of glass, films having suitable barrier properties such as alternating stacks of polymer and dielectric as disclosed in, for example, WO 01/81649 or an airtight container as disclosed in, for example, WO 01/19142.
  • a getter material for absorption of any atmospheric moisture and/or oxygen that may permeate through the substrate or encapsulant may be disposed between the substrate and the encapsulant.
  • At least one of the electrodes is semi-transparent in order that light may be absorbed (in the case of a photoresponsive device) or emitted (in the case of an OLED).
  • the anode is transparent, it typically comprises indium tin oxide. Examples of transparent cathodes are disclosed in, for example, GB 2348316.
  • FIG. 1 illustrates a device wherein the device is formed by firstly forming an anode on a substrate followed by deposition of an electroluminescent/light-emissive layer and a cathode, however it will be appreciated that the device of the invention could also be formed by firstly forming a cathode on a substrate followed by deposition of an electroluminescent layer and an anode.
  • a monochrome display may be provided by an array of pixels containing the same coloured electroluminescent material.
  • a full colour display may be provided with red, green and blue sub-pixels.
  • red electroluminescent material is meant an organic material that by electroluminescence emits radiation having a wavelength in the range of 600-750 nm, preferably 600-700 nm, more preferably 610-650 nm and most preferably having an emission peak around 650-660 nm.
  • green electroluminescent material is meant an organic material that by electroluminescence emits radiation having a wavelength in the range of 510-580 nm, preferably 510-570 nm.
  • blue electroluminescent material is meant an organic material that by electroluminescence emits radiation having a wavelength in the range of 400-500 nm, more preferably 430-500 nm.
  • Polymer A may be a charge transporting polymer containing, for example, a fluorene type monomer unit, a triaryl amine unit (such as TFB) and a vinyl functionalised monomer unit.
  • Polymer B may be an emissive polymer or a different charge transporting polymer, again, for example, based on fluorene. Some of the monomer units may be functionalised with a BOB unit.
  • the second emitting polymer can be made from the following monomers using the same method:
  • the organic layer thus formed can then be heated at an appropriate temperature to initiate cross-linking of the vinyl groups (this begins to occur at above 70° C. and is largely complete at 150° C.).
  • the organic layer may then be further heated up to the cross-linking temperature of the other functionality (in this case the BCB unit, ⁇ 200° C.). This results in an interpenetrating network (though the BCB units are likely to be less discriminate in their reactivity).

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US12/444,102 2006-10-10 2007-10-09 Opto-electrical devices and methods of making the same Expired - Fee Related US8124965B2 (en)

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GBGB0620045.5A GB0620045D0 (en) 2006-10-10 2006-10-10 Otpo-electrical devices and methods of making the same
GB0620045.5 2006-10-10
PCT/GB2007/003832 WO2008044003A1 (en) 2006-10-10 2007-10-09 Opto-electrical devices and methods of making the same

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